{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,25]],"date-time":"2026-09-25T08:13:52Z","timestamp":1790324032853,"version":"4.1.0"},"reference-count":119,"publisher":"Wiley","issue":"28","license":[{"start":{"date-parts":[[2015,5,27]],"date-time":"2015-05-27T00:00:00Z","timestamp":1432684800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2015,7,6]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>An efficient zinc(II)\u2010catalyzed alkyne oxidation\/C\uf8ffH functionalization sequence was developed, thus leading to highly site\u2010selective synthesis of a variety of isoquinolones and \u03b2\u2010carbolines. Importantly, in contrast to the well\u2010established gold\u2010catalyzed intermolecular alkyne oxidation, over\u2010oxidation can be completely suppressed in this system and the reaction most likely proceeds by a Friedel\u2013Crafts\u2010type pathway. Mechanistic studies and theoretical calculations are described.<\/jats:p>","DOI":"10.1002\/anie.201502553","type":"journal-article","created":{"date-parts":[[2015,5,27]],"date-time":"2015-05-27T16:20:52Z","timestamp":1432743652000},"page":"8245-8249","source":"Crossref","is-referenced-by-count":172,"title":["Zinc\u2010Catalyzed Alkyne Oxidation\/C\uf8ffH Functionalization: Highly Site\u2010Selective Synthesis of Versatile Isoquinolones and \u03b2\u2010Carbolines"],"prefix":"10.1002","volume":"54","author":[{"given":"Long","family":"Li","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bo","family":"Zhou","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yong\u2010Heng","family":"Wang","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chao","family":"Shu","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yi\u2010Fei","family":"Pan","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xin","family":"Lu","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Long\u2010Wu","family":"Ye","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2015,5,27]]},"reference":[{"key":"e_1_2_2_1_2","unstructured":"For recent selected reviews see:"},{"key":"e_1_2_2_2_2","volume-title":"Modern Rhodium\u2010Catalyzed Transformations","author":"Doyle M. P.","year":"2005"},{"key":"e_1_2_2_3_2","first-page":"203","volume-title":"Topics in Organometallic Chemistry, Vol.\u200510","author":"Doyle M. P.","year":"2004"},{"key":"e_1_2_2_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar300013t"},{"key":"e_1_2_2_5_2","doi-asserted-by":"publisher","DOI":"10.1039\/c0cs00217h"},{"key":"e_1_2_2_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr900239n"},{"key":"e_1_2_2_7_2","doi-asserted-by":"publisher","DOI":"10.1039\/b901170f"},{"key":"e_1_2_2_8_2","unstructured":"For recent examples see:"},{"key":"e_1_2_2_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol5011505"},{"key":"e_1_2_2_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/cs4001656"},{"key":"e_1_2_2_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol050003m"},{"key":"e_1_2_2_12_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200400237"},{"key":"e_1_2_2_13_2","unstructured":"For reviews see:"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar4001839"},{"key":"e_1_2_2_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar400181x"},{"key":"e_1_2_2_16_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201100148"},{"key":"e_1_2_2_16_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201100148"},{"key":"e_1_2_2_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja070789e"},{"key":"e_1_2_2_18_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200701449"},{"key":"e_1_2_2_18_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200701449"},{"key":"e_1_2_2_19_2","unstructured":"For recent selected examples see:"},{"key":"e_1_2_2_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja505945d"},{"key":"e_1_2_2_21_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201403015"},{"key":"e_1_2_2_21_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201403015"},{"key":"e_1_2_2_22_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201310146"},{"key":"e_1_2_2_22_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201310146"},{"key":"e_1_2_2_23_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4CC01059K"},{"key":"e_1_2_2_24_2","doi-asserted-by":"publisher","DOI":"10.1039\/c4cc00739e"},{"key":"e_1_2_2_25_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201300996"},{"key":"e_1_2_2_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja4085385"},{"key":"e_1_2_2_27_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201304700"},{"key":"e_1_2_2_27_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201304700"},{"key":"e_1_2_2_28_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201303016"},{"key":"e_1_2_2_28_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201303016"},{"key":"e_1_2_2_29_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201301601"},{"key":"e_1_2_2_29_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201301601"},{"key":"e_1_2_2_30_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201210313"},{"key":"e_1_2_2_30_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201210313"},{"key":"e_1_2_2_31_2","unstructured":"\u00a0"},{"key":"e_1_2_2_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja4047069"},{"key":"e_1_2_2_33_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201406747"},{"key":"e_1_2_2_33_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201406747"},{"key":"e_1_2_2_34_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201102561"},{"key":"e_1_2_2_34_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201102561"},{"key":"e_1_2_2_35_2","unstructured":"For rhodium\u2010catalyzed metallonitrene\u2010initiated alkyne oxidation cascades see:"},{"key":"e_1_2_2_36_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201301087"},{"key":"e_1_2_2_36_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201301087"},{"key":"e_1_2_2_37_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja809078d"},{"key":"e_1_2_2_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja7111788"},{"key":"e_1_2_2_39_2","unstructured":"For recent reviews on ynamide reactivity see:"},{"key":"e_1_2_2_40_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar400193g"},{"key":"e_1_2_2_41_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr100003s"},{"key":"e_1_2_2_42_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200905817"},{"key":"e_1_2_2_42_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200905817"},{"key":"e_1_2_2_43_2","unstructured":"\u00a0"},{"key":"e_1_2_2_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol4007629"},{"key":"e_1_2_2_45_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201300162"},{"key":"e_1_2_2_46_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2cc33030j"},{"key":"e_1_2_2_47_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja208150d"},{"key":"e_1_2_2_48_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201102581"},{"key":"e_1_2_2_48_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201102581"},{"key":"e_1_2_2_49_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201004647"},{"key":"e_1_2_2_49_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201004647"},{"key":"e_1_2_2_50_2","unstructured":"For such a gold\u2010catalyzed oxidative cyclization which is limited to terminal alkynes or electron\u2010deficient internal alkynes see:"},{"key":"e_1_2_2_51_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201301015"},{"key":"e_1_2_2_51_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201301015"},{"key":"e_1_2_2_52_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201107561"},{"key":"e_1_2_2_52_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201107561"},{"key":"e_1_2_2_53_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2cc31972a"},{"key":"e_1_2_2_54_2","unstructured":"For recent reviews on zinc catalysis see:"},{"key":"e_1_2_2_55_2","doi-asserted-by":"publisher","DOI":"10.1021\/cs300685q"},{"key":"e_1_2_2_56_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201200547"},{"key":"e_1_2_2_57_2","unstructured":"For our efforts on the gold\u2010catalyzed intermolecular alkyne oxidation see:"},{"key":"e_1_2_2_58_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4SC00983E"},{"key":"e_1_2_2_59_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4CC05115G"},{"key":"e_1_2_2_60_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4CC03565H"},{"key":"e_1_2_2_61_2","doi-asserted-by":"publisher","DOI":"10.1039\/C3CC49238A"},{"key":"e_1_2_2_62_2","unstructured":"For details please see the Supporting Information."},{"key":"e_1_2_2_63_2","unstructured":"For acid\u2010promoted oxidative cyclizations see:"},{"key":"e_1_2_2_64_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201304813"},{"key":"e_1_2_2_64_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201304813"},{"key":"e_1_2_2_65_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201205062"},{"key":"e_1_2_2_65_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201205062"},{"key":"e_1_2_2_66_2","volume-title":"The Isoquinoline Alkaloids, Vol.\u20051","author":"Bentley K. W.","year":"1998"},{"key":"e_1_2_2_67_2","unstructured":"CCDC\u20051032701 (5\u2009c) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre viawww.ccdc.cam.ac.uk\/data_request\/cif."},{"key":"e_1_2_2_68_2","unstructured":"\u00a0"},{"key":"e_1_2_2_69_2","doi-asserted-by":"publisher","DOI":"10.1039\/b809890e"},{"key":"e_1_2_2_70_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2003.12.019"},{"key":"e_1_2_2_71_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)01431-9"},{"key":"e_1_2_2_72_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(00)00725-0"},{"key":"e_1_2_2_73_2","unstructured":"\u00a0"},{"key":"e_1_2_2_74_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201007624"},{"key":"e_1_2_2_74_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201007624"},{"key":"e_1_2_2_75_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja1033952"},{"key":"e_1_2_2_76_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja100041e"},{"key":"e_1_2_2_77_2","unstructured":"For reviews see:"},{"key":"e_1_2_2_78_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr030692k"},{"key":"e_1_2_2_79_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr010212u"},{"key":"e_1_2_2_80_2","first-page":"1179","volume":"14","author":"Charifson P. S.","year":"1989","journal-title":"Drugs Future"},{"key":"e_1_2_2_81_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol1004356"},{"key":"e_1_2_2_82_2","doi-asserted-by":"publisher","DOI":"10.1002\/asia.200900470"},{"key":"e_1_2_2_83_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2006.03.005"},{"key":"e_1_2_2_84_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm00367a006"},{"key":"e_1_2_2_85_2","unstructured":"K. D.Hargrave C. K.Miao T. P.Parks I. F.Potocki R. J.Snow PCT Int. Appl. WO 9806719A1 1998."},{"key":"e_1_2_2_86_2","unstructured":"\u00a0"},{"key":"e_1_2_2_87_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(03)00824-X"},{"key":"e_1_2_2_88_2","doi-asserted-by":"publisher","DOI":"10.1021\/np50105a018"},{"key":"e_1_2_2_89_2","unstructured":"For the generation of zinc carbenoids from alkynes see:"},{"key":"e_1_2_2_90_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol502848n"},{"key":"e_1_2_2_91_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4CC03960B"},{"key":"e_1_2_2_92_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201402513"},{"key":"e_1_2_2_93_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201203914"},{"key":"e_1_2_2_93_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201203914"},{"key":"e_1_2_2_94_2","unstructured":"For relevant examples of gold\u2010catalyzed alkyne oxidations which do not involve gold carbene intermediates see:"},{"key":"e_1_2_2_95_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201407717"},{"key":"e_1_2_2_95_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201407717"},{"key":"e_1_2_2_96_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201410056"},{"key":"e_1_2_2_96_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201410056"},{"key":"e_1_2_2_97_2","unstructured":"When the reaction was performed in the presence of 5\u2005equiv of D2O >85\u2009% deuterium incorporation at the \u03b1\u2010position was observed and further supports our proposed mechanism. Please see the Supporting Information for full details."}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fanie.201502553","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201502553","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,10,16]],"date-time":"2023-10-16T17:20:29Z","timestamp":1697476829000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.201502553"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2015,5,27]]},"references-count":119,"journal-issue":{"issue":"28","published-print":{"date-parts":[[2015,7,6]]}},"alternative-id":["10.1002\/anie.201502553"],"URL":"https:\/\/doi.org\/10.1002\/anie.201502553","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2015,5,27]]}}}